1,2-asymmetric induction in dianionic-allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds.

被引:25
作者
Hanessian, S [1 ]
Margarita, R [1 ]
Hall, A [1 ]
Luo, XH [1 ]
机构
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
关键词
allylation; asymmetric induction; amino acids and derivatives; peptide analogs/mimetics;
D O I
10.1016/S0040-4039(98)00899-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied; Synthetic applications and potential utility in peptidomimetic design are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5883 / 5886
页数:4
相关论文
共 44 条
[41]  
UZAR HC, 1991, SYNTHESIS-STUTTGART, P526
[42]  
Williams R. M., 1989, Synthesis of Optically Active AE-Amino Acids
[43]  
WITTENBERGER SJ, 1993, SYNLETT, P795
[44]   Highly stereoselective kinetic enolate formation: Steric vs electronic effects [J].
Xie, LF ;
Isenberger, KM ;
Held, G ;
Dahl, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7516-7519